biostudies-literatureIkai TDivision of Materials ResearchJapan Society for the Promotion of Science20483-20487https://www.ebi.ac.uk/biostudies/studies/S-EPMC9080901biostudies-literatureUnknown8(37)A pair of optically active triptycene derivatives ((<i>R</i>,<i>R</i>)- and (<i>S</i>,<i>S</i>)-8) with a distorted cyclic structure were synthesized <i>via</i> an intramolecular etherification and evaluated as a novel chiral selector for high-performance liquid chromatography. The (<i>R</i>,<i>R</i>)- and (<i>S</i>,<i>S</i>)-8-based chiral stationary phases (CSPs) were found to be particularly effective in the resolution of axially chiral biaryl compounds. The importance of the distorted cyclic structure present in 8 for chiral recognition was demonstrated by comparisons with the corresponding non-cyclic model compound ((<i>R</i>,<i>R</i>)-9), which did not display enantioselectivity in the separation of the test racemates.RSC advancesOptically active distorted cyclic triptycenes: chiral stationary phases for HPLC.PMC9080901R270217K05875DMR-1410718Nagata NAwata SMizuno MWada YIkai TMaeda KSwager TMfalseOptically active distorted cyclic triptycenes: chiral stationary phases for HPLC.A pair of optically active triptycene derivatives ((<i>R</i>,<i>R</i>)- and (<i>S</i>,<i>S</i>)-8) with a distorted cyclic structure were synthesized <i>via</i> an intramolecular etherification and evaluated as a novel chiral selector for high-performance liquid chromatography. The (<i>R</i>,<i>R</i>)- and (<i>S</i>,<i>S</i>)-8-based chiral stationary phases (CSPs) were found to be particularly effective in the resolution of axially chiral biaryl compounds. The importance of the distorted cyclic structure present in 8 for chiral recognition was demonstrated by comparisons with the corresponding non-cyclic model compound ((<i>R</i>,<i>R</i>)-9), which did not display enantioselectivity in the separation of the test racemates.2018-01-01T00:00:00Z2018 Jun2025-04-04T20:50:24.421Z2025-02-19T03:25:11.255ZS-EPMC90809013554236510.1039/c8ra04434a